


The Red Hole

by samflower



Series: 100 Kink Challenge [2]
Category: Supernatural
Genre: 100 kink challenge, Anal Gaping, Anal Sex, Anonymity, Anonymous Sex, Bottom Dean, Dean in Hell, Demons, Double Anal Penetration, Double Penetration, Double Penetration in Two Holes, Forced Ejaculation, Forced Orgasm, Forced Prostitution, Gangbang, Gay Dean Winchester, Gay Sex, Graphic Description, Hell, Intense, Kink, M/M, Male Homosexuality, Rape/Non-con Elements, Semi-Public Sex, Sex Slave, Sex Slave Dean, Slow Updates, Super intense, Torture, Violent Sex, reader discretion advised
Language: English
Status: Completed
Published: 2017-06-06
Updated: 2017-06-06
Packaged: 2018-11-09 20:15:11
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 2,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11112033
Author URL: https://archiveofourown.org/users/samflower/pseuds/samflower
Summary: Dean's in Hell and he just wants the torture to end, so when he begs to the wrong demon, Dean ends up in a pretty sticky situation with his body being traded for cross-roads deals.INCLUDES INTENSE RAPE/NON-CON ELEMENTS. PLEASE READ AT YOUR OWN DISCRETION.





	The Red Hole

**Author's Note:**

> Hello! Just a quick note:
> 
> This story won't be written for some months to come. It was just a first chapter that I posted here to build momentum while I continue writing the rest. I kind of want to finish this one before I continue it, as I don't yet know exactly where it's going to go, but I do have some ideas. So, thank you so much for your patience, and if you like this first chapter, please subscribe that way you'll be notified as soon as the next chapters come out.

“Please… make it stop,” Dean’s eyes had nearly rolled into the back of his head by this point. His voice, once deep and gruff, was now flat and without feeling. Most of the time intense torture stopped hurting, the brain just blocked it out as a way to deal with it, especially when death wasn’t an option. Dean assumed being dead already meant that this rule came into play now more so than ever. The pain, God, that excruciating pain. It never stopped. Not once in the countless days, weeks, months he had been there.

“You want it to stop, huh?” The demon’s eyes glowed with a defiance and malice, the likes of which Dean had never seen before. The demon dragged the dull blade up Dean’s leg slowly, not cutting, but warning Dean to stay still and keep his mouth shut. Dean, whose eyes were nearly swollen shut 24/7 managed to crack them open ever-so-slightly to get a small peek at the demon who had been cutting him up for however long he had been stuck in this God forsaken place.

Deans eye exploded into pain once more as the demon hit him square on. “You going to beg like a little bitch, I guess we treat you like a little bitch,” Dean could hear the malice and psychopathy dripping from the edged tongue of the demon standing over him. God, Dean wanted nothing more than to go back to his brother, see Sam’s stupid hair and his stupid grin and his stupid height. He wanted to sit in the front seat of his baby. He wanted to taste the sweet taste of a pie or hear some shitty hair rock. Dean missed anything that wasn’t pain, darkness, and screaming.

The demon disappeared for a long moment. It was the most relief Dean had in nearly a week--or what felt like a week, anyway. Suddenly, Dean felt his body falling. His arms and legs flailed out to catch himself, but he knew that even if you could, he’d be too weak to do so. It was less than an inch drop before Dean landed on the springy bed below him. His body bounced slightly causing the mattress to squeak and squeal. Dean’s body felt like it was on fire, this had been the most comfortable position he had been in in God knows how long.

Dean’s breathing was ragged and slow as the demon, and what sounded like one other circled the side of the bed to get a good look at him. “Well, would you look at that… Do you know how many deals someone would sacrifice to torture this sonofabitch?” The demon’s voice was gruff and masculine. Another one sounded from behind the second one.

“Do you know how many deals I would give up to fuck this sonofabitch?” The third one mimicked the first and Dean nearly puked when he realized what he had gotten himself into. Were they going to fuck him until he was red and raw and then discard him for some other demon to use? Were they going to sell him for deals for whoever wanted to use him--

“Fifteen deals a demon and they get to stick their cock in the Winchester’s tight asshole for five minutes,” one of the demons bargained. The others seemed to think it over for a long, long moment and Dean’s heartbeat quickened inside of his chest, nearly pounding against his ribcage. He hadn’t been more _terrified_ since he’d gotten here in the first place.

Dean wasn’t gay! How were they going to do- Dean’s thoughts were stopped when he felt a cold breeze blow across his entire body. His hands were suddenly cuffed to the bed post, not that he’d dare try and move anyway. He was dead, it’s not like he had anywhere to escape to, even if he wanted that more than his own life. The room was freezing and it smelled musty as if it was abandoned.

“Sounds fine to me, you?” One demon asked the other demons. If Dean had been in any other setting, he would have laughed at the typical New York accent and phrasing, but Dean could barely bring himself to stop screaming and crying for two seconds, let alone smile or _laugh_.

“Yeah, I’ll let everyone know our terms.” Dean heard the rustling of clothes and he instantly started to sob. One of the demons walked over to him and sighed as if Dean had disgraced the family.

“Dean, Dean, Dean… what more do you _want_ from us?” The demon was angry, which only made Dean’s heart throb faster with every word he enunciated with rage. The demon grabbed Dean roughly by the ankle and lifted his broken, battered leg up high. Dean screamed, he wasn’t sure how much more his body could take, not that it mattered, it’s not like he could die when he was already dead. He bent at the midsection, his ass exposed in the freezing air. A hand pried apart his ass cheeks, slipping inside his warmth to feel at his newly exposed, and soon to be shredded, hole.

Dean’s breath caught in his throat, nononono! If there is a God, please… please don’t let them do this to me! Streams of tears ran quickly down Dean’s face, he was choking on sobs now, unable to contain them all. Dean wasn’t usually the type to break down and cry. He had never fallen apart like this before, but that’s when they kept the torture, knife, Dean, blood not dick fucking Dean in the asshole. The demon threw Dean’s battered leg down, causing Dean to let out another shrill shriek of pain. 

“Help me flip him. We need to get him ready for the others,” the two demons flipped Dean’s body. It was in pieces, held together by failing skin and muscle, which was almost ripped away too. Dean heard the flip of a knife and sobbed softly into the disgusting smelling mattress below him. They carved something into his once supple, soft ass. It felt like they had carved-

“Fifteen souls. No haggling with the price,” one of the demons tutted. They sounded proud of themselves, like they had just had the most brilliant idea of branding Dean in this way.  
Within minutes, Dean had started to hear the rustle of clothes behind him, feel the gaze of demons checking out his bare, battered body. Dean nearly retched at the feeling of dread and shock that filled him. He dry heaved a bit when one of the demons was heard to be dealing the fifteen souls to his captives.

Just relax… The voice almost wasn’t his own. How was he supposed to relax? He couldn’t do this for the rest of eternity, taking demon cock in his tight, virgin hole!

Two of the demons were brought forward and doors were closed behind them. He could hear their footsteps as well as belts being unbuckled, pants being pushed down. Dean was nearly hyperventilating at this point. He had never felt like this before, never felt so damn used. Never felt so damn helpless to himself. What the fuck could he do besides lie there and take the cocks like a good little bitch? It’s not like he could fight his way out, there was no way for him to get back to the top. He couldn’t pray, he had tried that for months now. He was stuck here.

He heard the two demons getting closer to them. One was behind him, near his ass and one was in front of his face. The one by his face grabbed Dean’s hair and yanked his head back so far the muscles in his neck felt like they were about to rip themselves to shreds. His swollen eyes watered beyond the tears and he could hear the demon snigger to himself. They conversed among themselves about Dean for a long moment but Dean’s heart was beating too loudly for him to hear them. He could feel the blood rushing through his head, pounding against his eardrums.

The demon must have said something to him that Dean didn’t hear because next thing he knows, he’s being lifted up by his neck, his back being arched so far it felt like it was going to break. “Open your mouth, cockslut!” The demon’s voice boomed and the other demon slide his hands up and down the backs of Dean’s thighs. It took Dean a long moment and a lot of force on Dean’s airways for Dean to open his mouth. He did it meekly at first, but the demon had other plans. He shoved his hand into Dean’s mouth and yanked his jaw down and out of place with a sickening crack. Dean’s jaw was stuck like that until the demon pushed it back up to the perfect position. The pain was agonizing. The demon pushed Dean’s head down as the other demon spread Dean’s cheeks far enough to see his tight, virgin hole. One of the demons fingers began working it slowly, testing the waters to see how Dean would respond to taking a cock after no preparation.

With a harsh smack in the face, the demon entered Dean’s wet, untrained mouth. “Bite me and I fuck you with my knife, bitch,” one of the two demons snarled at him. The demon’s tip pushed in past Dean’s swollen lips and Dean nearly gagged.

The smell of the demon’s dick was intense, everything about it was intense. Especially when the demon behind him, with no warning lined himself up and plunged into Dean with just a little bit of spit and precum to help with the friction. Dean felt like he was being split in half. His head spun and he stopped sucking on the length in his mouth to let out a loud scream of agony.  
The scream earned him a hard smack from the demon in front of him as the demon behind him began sloppily jerking his hips forwards and backwards, guttural moans escaping his mouth. Dean could feel the blood pouring from his torn hole. At least it acted as an extra lubricant for the demon’s larger than average girth. Through tears and darkness, Dean’s mouth found the demon’s shaft again, taking the whole thing down his throat this time. He tried his hardest not to throw up when the demons hips began to jerk violently, thrusting himself in and out of Dean’s broken mouth.

Dean could feel the broken bones in his legs grinding together furiously as the demon ravaged his bloody, gaping asshole with loud, animalistic screams of pleasure. In its throes of pleasure, it ripped Dean’s hips back against its own, the sound of balls slapping on skin barely audible over the two demons growls of dominance and superiority. They had been the first to taken Dean and they could feel it. 

The demon in front of him grabbed Dean’s hair violently and fucked himself down Dean’s throat before finally blowing his loud all over the back of Dean’s throat and tongue. “Swallow it, every last drop, little cockslut,” the demon’s voice was terrifying and Dean was nearly delirious from the pain. He swallowed obediently, almost without thinking about it. His cheeks were flushed and bloody. He knew there were more demons he would have to take, with how quickly these two had arrived, there had to have been quite the number. His entire back half had now gone numb, for which he was grateful. All he felt was an intense pressure as the demon in his ass picked up speed, slamming into him with a great, sloppy force as he neared his own orgasm.  
Dean knew he was about to orgasm as well. He didn’t want to, Hell, he didn’t even know how he could. His body must have been reacting to all of the stimuli, because as soon as the demon shredding his asshole to pieces gave a shout as he orgasmed, so did Dean. Dean turned into a mewling mess of tears, snot, blood, and cum. The mattress was a mess and so was Dean, as if he hadn’t been in the first place.

In the next eight months, Dean had made his original handlers fortune. He had taken cock after cock after cock. Hell, he’d even taken more than one cock at a time. Each time, they’d renew his virigin hole and make him relive the same experience over and over again. When Dean wasn’t taking cocks, he was being beaten, caned, flogged, and things Dean couldn’t even imagine.

By the time he was lifted from Hell--to which, he later thanked an angel named Castiel for by trying to take his cock--he knew nothing but taking cock.

They did it, Hell broke _Dean Winchester_.

**Author's Note:**

> I hope you guys liked that really intense scene there, if you'd like more like this one, please check out my 100 Kink Challenge where I will be posting more stories just like this one.


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